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Boston, MA

Sailing

Browse by SailingSailing is a well known local and tourist activity for Boston.  It is the perfect way to do some Harbor sightseeing by boat.  Join us with our professional crew and take to the waters to sail Boston Harbor aboard Schooner Adirondack III.

Let our amazing crew dazzle you with their sailing skills and top-notch customer service. Boston sailing is fun, but sailing and sightseeing is the most wonderful way to experience Beantown.

Sail past Boston’s Waterfront to see the U.S.S. Constitution, Fort Independence (named by George Washington), Marriott Custom House Tower, U.S.S Cassin Young, and see the steeple of the Old North Church in Boston’s North End. This city skyline and local Islands are a must see when visiting (or just needing an escape from the city) and you can enjoy all of these sites with a glass of wine or Champagne in hand aboard our 80-foot schooner, Adirondack III.  We not only offer the most premium sailing experience in Boston, but have 5 star reviews for our service.  

Boston Day Sail

Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise. Our classic afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speed.

  Duration: 1.5 hrs OR 2 hrs   Boat: Adirondack III   Cost: Adult $45 for 1.5 hrs | Adult $48 for 2 hrs

Boston Sunset Sail

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

  Duration: 2 hrs   Boat: Adirondack III   Cost: Adult $58

Boston City Lights Sail

For the ultra-romantic choose our City Lights Sail aboard our sailboat. This serene sail allows you to experience Boston with peaceful tranquility. Enjoy the evening sea breeze swirling around you and all of Boston’s twinkling lights as your backdrop. Take-in the shimmering city of Boston on a smooth and gentle sail. Blankets are available to guest upon request on chilly nights. Cozy up with a loved one on the decks of our beautiful schooner.

  Duration: 1.5 hrs   Boat: Adirondack III   Cost: Adult $40

Boston USS Constitution Turnaround Sail

U.S.S. Constitution Turnaround Sail aboard Schooner Adirondack III

Join us for the 2.5-3 hour long sail on July 4th to view the turnaround of the U.S.S. Constitution, the oldest (1797) actively commissioned naval vessel in the world. Experience this yearly event like you never have before aboard Adirondack III, a classic 80-foot pilot schooner. She features comfortable seating and a brisk ride, as we are able to view the turnaround of the U.S.S. Constitution. You won’t want to miss this truly unique and special event! The turnaround takes place once a year to celebrate our nation’s birthday. The U.S.S. Constitution will sail out into Boston Harbor where she’ll exchange a 21-gun salute with Castle Island’s Fort Independence. While aboard enjoy complimentary pastries, bagels, and muffins with our continental breakfast.  (Continental breakfast includes: Assorted Pastries, Scones, and Muffins, Jalapeño Cheese Bagels with Cream Cheese, Fresh Seasonal Fruit, Yogurt and Granola)

  Duration: 2.5 - 3 hrs   Boat: Adirondack III   Cost: Adults $130

Labor Day Fireworks Cruise Aboard Adirondack III

What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard beautiful Adirondack III for a magnificent Labor Day cruise. This 1.5-hour cruise offers guests the opportunity to soak up Boston’s colorful fireworks display from an awesome vantage point, practically right underneath them and out on the water! (The event does not sail and offers spectacular views of the fireworks)

  Duration: 2 hrs   Boat: Adirondack III   Cost: $75

Winthrope Fireworks Cruise with Classic Harbor Line

Winthrop 4th of July Fireworks Cruise and Sail on Adirondack III

Don’t want to deal with all the traffic crowds and hype surrounding the 4th of July, but still want to celebrate and enjoy the patriotic holiday? Step aboard the Adirondack III for a cruise to Winthrop to watch the fireworks and then sail back to Boston at the end. Sip on Champagne and enjoy this magical evening with the best seats in the house! 

  Duration: 3 - 3.5 hrs   Boat: Adirondack III   Cost: Adult $80 | Child $60

Boston Harbor Labor Day Fireworks Cruise

Illuminate the Harbor Fireworks Sail aboard Schooner Adirondack III

What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard the historic and beautiful Adirondack III for Illuminate the Harbor Fireworks hosted by Boston Harbor Now.  This **1.5-hour cruise** offers guests the opportunity to soak up Boston’s colorful fireworks display from an elegant and relaxing vantage point out on the water. The Adirondack III is a brilliant 80-foot long pilot schooner modeled after similar boats built in the 1890s. Unlike those older boats, it is built to provide ample space to accommodate each and every one of its guests, ensuring a comfortable and quality experience for anyone who boards.

  Duration: 1.5 hrs   Boat: Schooner Adirondack III   Cost: Adult $80 | Child $60

Boston Day Sail

Adirondack III 90-Minute Mimosa Day Sail

Our classic, 90-minute, afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speediness to boot.  Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise.

 

  Duration: 1.5 hrs   Boat: Adirondack III   Cost: Adult $45 | Child $28

Harborfest Fireworks & Lighted Boat Parade Cruise aboard Adirondack III

Get the fourth of July week started with a BANG! Step aboard the Adirondack III as we parade the harbor decorated in lights for the return of the Lighted Boat Parade in Boston Harbor. Wave to your fellow patriots on the shoreline as we cruise around and see the sites of Boston! Following our parade around the harbor enjoy a spectacular fireworks display on Boston Harbor.  Join us for two hour and thirty minute sail & cruise, followed by Harborfest Fireworks lighting up along Boston’s Waterfront.  In addition to a fantastic experience, this captivating Labor Day Fireworks Cruise will feature delicious, complimentary desserts, cheese and flatbreads, and sliced fruits.
  Duration: 2.75 hrs   Boat: Schooner Adirondack III   Cost: $130

Boston Pride Sunset Sail

Adirondack III Pride Sunset Sail

Experience a beautiful 2-hour Boston Harbor sunset sail on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III, a classically styled, 80-foot pilot schooner. Adirondack III is the fastest and most elegant schooner in Boston Harbor. She offers a smooth and gentle sailing experience to her passengers as well as top-notch customer service by her captain and crew. Enjoy a comfortable and relaxing ride for you and your loved ones. Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a stellar vessel.
  Duration: 2 hrs   Boat: Schooner Adirondack III   Cost: Adult $58

Boston Pride Day Sail

Adirondack III Pride Day Sail

Our classic 2-hour or 1.5 hour afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speediness to boot. This sail is great for families who want to get out and see the sights. Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise!
  Duration: hoose a 1.5hr or 2hr sailing option   Boat: Schooner Adirondack III   Cost: Adults $48 or $45

Harbor Fireworks Cruise aboard Schooner Adirondack III off of Spectacle Island

What better way to celebrate summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard the historic and beautiful Adirondack III for Illuminate the Harbor Fireworks off of Spectacle Island. This 1.5-hour cruise offers guests the opportunity to soak up Boston’s colorful fireworks display from an elegant and relaxing vantage point out on the water. The Adirondack III is a brilliant 80-foot long pilot schooner modeled after similar boats built in the 1890s.  Please note that we may not be able to raise sail for the fireworks due to crowding in the harbor. If time permits, we may do some sailing after the fireworks.

  Duration: 1.5 hrs   Boat: Schooner Adirondack III   Cost: $65